A Straightforward Hetero-Diels-Alder Approach to (2-ambo,4 ' R,8 ' R)-alpha/beta/gamma/delta-4-Thiatocopherol

作者：Menichetti Stefano^*; Amorati Riccardo; Bartolozzi Maria Grazia; Pedulli Gian Franco; Salvini Antonella; Viglianisi Caterina

来源：European Journal of Organic Chemistry, 2010, (11): 2218-2225.

DOI：10.1002/ejoc.200901493

• Vitamins
• Tocopherols
• Sulfur heterocycles
• Antioxidant
• Cycloaddition

A simple and original inverse electron demand hetero-Diels- Alder reaction has been successfully applied to the synthesis of (2-ambo,4'R,8'R)-alpha/beta/gamma/delta-4-thiatocopherol. Commercially available methyl hydroquinones and (2E,7R,11R)-(+)-phytol were exploited for the preparation of the ortho-thioquinones, acting as electron-poor dienes, and of the proper 1,3-diene used as dienophile, respectively. The benzoxathiine cycloadducts, with the required tocopherol-like skeleton, were obtained with complete control of regio and chemoselectivity. The antioxidant activity of 4-thiatocopherols was measured and rationalized in comparison with that of the corresponding natural components of Vitamin E.

• 出版日期2010-4